


kinktober 5 - stress relief on the job

by skinsharpenedteeth (Skinsharpenedteeth)



Series: kinktober 2020 [5]
Category: Teen Wolf (TV)
Genre: Alternate Universe - Office, Anal Fingering, Anal Sex, Clothed Sex, Kinktober, M/M, Office Sex, Plot What Plot/Porn Without Plot, Prostitution, Size Kink, Smut
Language: English
Status: Completed
Published: 2020-10-16
Updated: 2020-10-16
Packaged: 2021-03-08 18:20:11
Rating: Explicit
Warnings: No Archive Warnings Apply
Chapters: 1
Words: 2,484
Publisher: archiveofourown.org
Story URL: https://archiveofourown.org/works/27041131
Author URL: https://archiveofourown.org/users/Skinsharpenedteeth/pseuds/skinsharpenedteeth
Summary: Derek needs some help burning the midnight oil at work so he orders himself some company.
Relationships: Derek Hale/Stiles Stilinski
Series: kinktober 2020 [5]
Series URL: https://archiveofourown.org/series/1950628
Comments: 6
Kudos: 173





	kinktober 5 - stress relief on the job

**Author's Note:**

> Kinktober 5 (yes, I'm aware I'm woefully behind. Hush)
> 
> Prompts filled: Size kink, Office sex, Clothed/Unclothed sex, Prostitution

Stiles tapped his fingers nervously against his jean covered thighs as he waited for the elevator to reach the floor Erica had indicated in her text message. Apparently, some bored CEO needed a little late-night strange to keep the midnight oil burning and Stiles had been up in the rotation. He sighed through his nose as he thought about how long this might take since he had some homework to finish up before class in the morning. Why he’d signed up for early morning classes he’d never know…

The elevator dinged its arrival and the gold-plated doors swooshed open. He was looking at a white and grey marble lobby with glass doors that led into a cubicle farm with offices lining the outside walls. It looked claustrophobic to Stiles, especially if you were in one of the cubicles, but then again… you weren’t literally selling your ass to make rent money either so maybe he shouldn’t judge too harshly. Apparently natural sunlight was the tradeoff though and he wasn’t sure he’d be able to stand it. He stepped out of the elevator and dug his phone out of his back pocket. He looked down at the screen again to memorize the office he was looking for and pushed his way through the glass doors into the dark, silent office beyond. Even without the text directions he would’ve been able to find the office he wanted since it was in the farthest corner from the cubicles and it was the only one with the lights on. He mentally prepared himself and walked through open doorway.

One of the most beautiful men Stiles had laid eyes on was sitting at the large, dark cherry desk in the center of the office. Stiles could only see him in profile, but it was enough to understand that this guy was striking enough to never ever need to call for a midnight whore. He could probably just stick his dick out of the front door of the building, and someone would suck it for him for free. He was tan with dark, almost black hair that looked impossibly soft and a frame that said he hadn’t stopped working out since high school. He sat up straight at his L-shaped desk and was typing furiously on his computer, brows furrowed as he concentrated on the screen. Stiles could see leftover takeaway containers in his trash and the office smelled like coffee and Thai food. He came to the front of the desk and stood awkwardly for a moment, waiting for the man to take notice of him.

“Erica send you?” the man asked, voice serious but higher than Stiles expected. He’d asked this without stopping his work or glancing Stiles’ direction. Stiles cleared his throat before answering.

“Yeah, yep that’s me. What can I do for you?” Stiles asked, a little awkwardly. He didn’t know how he felt about being practically ignored like this. The man stopped typing and finally turned to look Stiles over. His cold hazel eyes traveled up and down Stiles’ body taking note of the too-tight jeans, the black batman tee two sizes too small and the red flannel. He looked wholly unimpressed, but Stiles figured if he’d wanted someone who would come in looking like they worked there, he should’ve negotiated for Jackson instead of the Young College Twink. His eyes came up to meet Stiles’ and he turned his chair and body to face him full on. He was wearing a slate colored suit with a cool toned button down underneath. His cufflinks glinted when they caught the light and his watch obviously could’ve paid for a semester or two of Stiles’ tuition. He was younger than forty, but how much younger Stiles couldn’t gauge except for his obviously high status within the office around them. When he spoke again, it startled Stiles a little since he’d been ruminating on exactly what type of work was done here.

“Strip for me,” he commanded, leaning back and interlacing his fingers in the air in front of him. Stiles looked at him for a second before stepping out of his shoes and pushing off his flannel. He had never mastered taking off his clothes in a sexy, alluring manner. He was a hooker, not a stripper. He let his clothes fall to the floor in a pile next to him until he was standing naked and almost shivering in the office air. The air conditioners hummed easily throughout the office and it was cool enough to make Stiles’ skin pimple. The walls were glass and he could see down into other buildings around them, but the windows were all dark. He wasn’t terribly worried about someone watching them. The man’s eyes swept over his body again.

“Get yourself hard,” he directed, still watching Stiles with a scrutinizing gaze that somehow caused a flush of heat to go through Stiles’ body. He didn’t know why he found this hot today with this man when normally this kind of exhibitionism wasn’t his bag, but he’d do as he was told. Some Johns liked to feel like you were there as an enthusiastic participant and would dock your fee if they saw you getting soft on them. Stiles could hold an erection while mentally going through biology flash cards, but getting there sometimes was a challenge.

He gripped himself loosely and started pulling on dick to get it hard. He closed his eyes, placed himself back in his bedroom in the apartment he shared with his best friend where no one could see him and he was doing this for fun. He brought his other hand up and roughly rubbed a thumb over one of his nipples. He pinched and pulled at the nub causing it to tighten and little jolts of desire began to run down to his cock. He left his nipple alone and started to knead and pull on his balls so he’d come to full hardness. When his cock felt solid enough, he let go and opened his eyes to look at the stranger. He was still watching him over his interlaced fingers, though his eyes were now darker, and Stiles could see the straining outline of his cock through his expensive suit pants.

“Come over here,” the stranger said, scooting further back from his desk and motioning to where he wanted Stiles to stand. He did as he was asked, leaning his naked ass against the cool wood of the desktop. He stared down at the stranger and waited. His gaze looked hungry now and it made Stiles cock throb with the need for one of them to do something to ease the pressure between his legs. The stranger unbuttoned his pants and pulled his pants and underwear down far enough to pull out his perfectly massive uncut penis. Stiles mouth watered just looking at it. It was fat and a little longer than normal, the mushroom tip peaking past the foreskin and already beading with precum.

“Are you prepped?” the man asked calmly as his hand slowly stroked over his girth, pulling the foreskin back from the head and then pushing it over, and Stiles had to swallow the flood of saliva in his mouth before answering.

“Yes,” he said, trying to sound unaffected, but his voice betrayed him by coming out high and breathy as he stared longingly at the man’s erection. He never got fucked by guys this good looking who were also packing a cock made for video.

“Then bend over the table and spread your legs for me,” he said, waiting for Stiles to comply. Stiles turned his body and bent over the table, pressing his heated flesh into the mirror-like finish, his nipples and cock jumping at the touch of cold against them. He widened his stance and waited patiently. He could hear a door opening behind him and soon felt the cool smearing of lube against his hole. Three fingers pushed into him without ceremony and he exhaled noisily at the unexpected feeling. He thought this beautiful, dark-haired Adonis would surely just jam his cock into him and start pounding away. He didn’t expect for him to finger fuck him first, but that is what he was doing. He pushed and withdrew his fingers in a smooth rhythm, twisting until Stiles let out a quick, electrified yelp when he dragged the pads over his prostate. As soon as that happened, the fingers disappeared leaving Stiles wondering if he’d somehow fucked up.

“You ready?” he heard the man ask from behind him. Stiles heard the creak of the chair and then he could feel the warm line of his body close behind his thighs and his stomach curled in delighted anticipation.

“What’s you name?” Stiles asked suddenly. He could feel the mental pause hit the room when he did, momentarily breaking the spell that they’d created together.

“Why?” the stranger asked, obviously nonplussed.

“So I know what to scream out when you’re railing me,” Stiles answered, daring to peak over his shoulder at the stranger. The man was giving Stiles a sexy smirk and shaking his head slightly.

“Derek. Call me Derek,” he answered after a beat. Stiles nodded and turned his body back onto the table.

“Okay Derek, come at me,” Stiles challenged, grinning at the huff of laughter he heard from behind him. The laughter didn’t last as Derek started pushing his fat cock past Stiles’ rim. The stretch almost ached, but it felt so, so good. Stiles felt full and getting fuller as the initial push to bury Derek inside of him seemed to last forever. Stiles was starting to sweat by the time he finally felt Derek’s balls resting against his perineum.

“Shit, fuck, okay now… Goddamn, you’re fucking big,” Stiles swore, turning his head to lean his forehead against the desktop as he waited for his muscles to relax a little around the thick shaft pushing at them.

“Fuckin’ flirt,” Derek answered derisively from behind him. Stiles took in a breath to reply but was stopped short as Derek pulled his hips back and gave a short, pointed thrust back into him, rocking Stiles’ body over the desk. Stiles grit his teeth and swore, but Derek kept going. He started with slow, shallow thrusts but before too long he was rocking back and snapping his hips forward, his cock splitting Stiles wide on the table. Stiles wanted to hate it, wanted to be professional and fake moan, fake pant, fake enjoy the situation, but since Derek had located his prostate he’d been nailing it with every other forward thrust and Stiles was just trying not to shoot before the customer did. He was leaking precum all over the desk beneath him and his cock slid through the mess with every jolt Derek gave his body, driving him fucking mad.

Derek was getting close; Stiles could tell by his stuttered breathing and the desperation starting to bleed into his thrusts. Stiles wondered if he’d unload inside him, paint his hole and make him clench to keep it in or if he was going to paint his skin in hot, wet stripes. He found he really didn’t care which Derek chose because with a few well-aimed thrusts, Derek had him coming apart onto his desk, cum flooding underneath him and smearing between his skin and the highly lacquered wood finish. It was like that was what he’d been waiting for too because Derek started to fuck Stiles faster as soon as the last drop was finished leaking from his spent cock. Stiles grit his teeth, rim tightening as much as it could as he forced himself to ride out the oversensitivity from his orgasm. Derek’s thrusts were almost violent, and Stiles knew he’d have a bruise across the top of his thighs tomorrow from the edge of his desk.

“Derek, fucking cum already!” he shouted, ready to crawl over the desk to get away from the animal nailing him from behind. It took half a dozen more thrusts, but then he felt the warm gush of fluid inside of him and Derek’s body stilled, a groan like he was dying pushing out of him as he emptied himself into Stiles’ body. They stayed where they were for a minute or two afterward, bodies thrumming with satiation and coming down from the high of arousal and completion. Finally, Derek pulled out and Stiles felt cold inside without him. He clenched and started pulling his muscles together to close up what felt like his gaping asshole. He felt Derek’s fingers slide up his taint through the liquid leaking out of him and push it back into him roughly.

“You’re making a mess,” he commented. Stiles heard the swoosh of air from his leather roller chair as Derek plopped down behind him with a loud exhalation. Slowly Stiles straightened his body, looking down to where he’d cum all over the desktop.

“If you think that’s a mess…” he started, gingerly sidestepping to get out from between Derek and his desk. He turned to see a smug look on Derek’s face as he eyed the streaks across the surface of his desk, marring the perfect mirror shined surface. Then he turned and looked at the same mess streaking Stiles stomach and groin.

“When you go to the restroom, grab a couple paper towels and clean this up. I’ll transfer your payment while you’re out,” Derek said, pointing past the office door towards the hallway. Stiles left the office still naked, not wanting to get his clothes messy with cooling jizz. He spent a couple minutes in the restroom with warm water and shitty pink office soap cleaning himself off before pulling a couple more and wetting them with the same to take back to Derek’s office. When he got back it was like he’d never been there except for the mess on the desk. Derek was back to staring at the computer screen and typing rapidly. Stiles eyed him for a minute before shrugging and cleaning his cum off the wood. When he was finished, he pulled his clothes on with his back to Derek.

“Think you can come again tomorrow night?” Derek asked into the silence between them. Stiles turned and saw that he was still not looking at him, but obviously his attention was divided because his keystrokes had slowly minutely as he waited for Stiles to answer.

“If you got the cash, I’ve got the ass,” Stiles drawled out easily.

“Good. Same time. If you bring a plug I’ll give you a bonus,” Derek answered. Stiles gave him a two-finger salute and turned to leave the office. Even though his body ached, and his ass felt hollow after such a fuck, he found he was excited about more than just the money when he returned the next day. He’d have to thank Erica for the job.

**Author's Note:**

> Would love to hear from you! Kudos, comments, and high fives are always a writers best friend!
> 
> come see me too at my [tumblr!](http://skinsharpenedteeth.tumblr.com)


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